1,2,3,4-Tetrahydro-7-nitroisoquinoline → Isoquinolin-7-amine

Participants

Reaction Steps

A mixture of 7-nitro-1,2,3,4-tetrahydro-isoquinoline (1.5 g, 8.38 mmole) and 10% Pd/C (300 mg) in diethylene glycol (5 mL) was reacted in a Smith Synthesizer under microwave radiation at 220° C. for 25 min. The resulting mixture was diluted with MeOH and filtered. The filtrate was concentrated and diluted with CH2Cl2, washed with sat. aq. NH4Cl and dried over Na2SO4. After filtration and concentration, the title compound was isolated through flash chromatography (eluted with CH2Cl2:MeOH 9:1) as an orange solid. MS: (ES+) 145 (M+H). Calc'd. for C9H8N2—144.07.

Provenance & Evidence